From Technical Efficiency to Economic Efficiency: Development of Aza-Friedel–Crafts Reaction Using Phosphoric Acid Immobilized in Glycerol as a Sustainable Approach
Abstract
:1. Introduction
2. Materials and Methods
2.1. General Information
2.2. General Sustainable Procedure for Environmentally Friendly and Atom Economical Synthesis of Dihydrobenzoxazinones
2.3. Method for Biological Activity Study
3. Results and Discussion
3.1. Sustainable and Practical Methodology
3.2. The Catalytic System Recycling
3.3. Biological Activity Study
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Entry | 1 | R1 | R2 | R3 | 2 | R4 | Product | Crude Yield (%) | Isolated Yield (%) |
---|---|---|---|---|---|---|---|---|---|
1 | 1a | H | H | H | 2a | H | 5a | 99 | 98 |
2 | 1b | H | F | H | 2a | H | 5b | 97 | 97 |
3 | 1c | H | Cl | H | 2a | H | 5c | 97 | 96 |
4 | 1d | H | H | Br | 2a | H | 5d | 95 | 93 |
5 | 1e | H | Me | H | 2a | H | 5e | 99 | 97 |
6 | 1f | H | H | Me | 2a | H | 5f | 95 | 93 |
7 | 1g | Me | H | H | 2a | H | 5g | 94 | 94 |
8 | 1a | H | H | H | 2b | Ph | 5h | 96 | 94 |
9 | 1b | H | F | H | 2b | Ph | 5i | 95 | 93 |
10 | 1c | H | Cl | H | 2b | Ph | 5j | 96 | 95 |
11 | 1e | H | Me | H | 2b | Ph | 5k | 97 | 96 |
12 | 1f | H | H | Me | 2b | Ph | 5l | 97 | 95 |
13 | 1a | H | H | H | 2c | p-ClC6H4 | 5m | 98 | 95 |
14 | 1b | H | F | H | 2c | p-ClC6H4 | 5n | 96 | 93 |
15 | 1e | H | Me | H | 2c | p-ClC6H4 | 5o | 95 | 94 |
16 | 1f | H | H | Me | 2c | p-ClC6H4 | 5p | 95 | 92 |
17 | 1a | H | H | H | 2d | p-MeC6H4 | 5q | 99 | 95 |
18 | 1b | H | F | H | 2d | p-MeC6H4 | 5r | 98 | 97 |
19 | 1f | H | H | Me | 2d | p-MeC6H4 | 5s | 99 | 96 |
Cycle | Time (h) | Crude yield | Cycle | Time (h) | Crude Yield |
---|---|---|---|---|---|
1 | 24 | 99 | 6 | 24 | 97 |
2 | 24 | 98 | 7 | 24 | 98 |
3 | 24 | 99 | 8 | 24 | 99 |
4 | 24 | 99 | 9 | 24 | 98 |
5 | 24 | 98 | 10 | 24 | 99 (96) b |
Compound | IC50 (μM) a | Compound | IC50 (μM) a | ||
---|---|---|---|---|---|
C6 | B16BL6 | C6 | B16BL6 | ||
5a | n.a. | 92.4 | 5k | 46.4 | 58.1 |
5b | 169.1 | 154.1 | 5l | 39.5 | 41.6 |
5c | 115.6 | n.a. | 5m | 15.4 | 63.2 |
5d | 232.5 | n.a. | 5n | 8.9 | 29.8 |
5e | 20.9 | n.a. | 5o | 18.7 | 24.2 |
5f | 81.0 | 100.2 | 5p | 19.4 | 25.7 |
5g | 149.2 | 70.9 | 5q | 42.3 | 68.4 |
5h | 127.7 | 193.3 | 5r | 44.2 | 37.4 |
5i | 58.3 | 75.7 | 5s | 19.6 | 90.9 |
5j | 42.2 | 94.3 | adriamycin | 18.8 | 96.7 |
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Tan, L.; Rahman, A. From Technical Efficiency to Economic Efficiency: Development of Aza-Friedel–Crafts Reaction Using Phosphoric Acid Immobilized in Glycerol as a Sustainable Approach. Sustainability 2017, 9, 1176. https://doi.org/10.3390/su9071176
Tan L, Rahman A. From Technical Efficiency to Economic Efficiency: Development of Aza-Friedel–Crafts Reaction Using Phosphoric Acid Immobilized in Glycerol as a Sustainable Approach. Sustainability. 2017; 9(7):1176. https://doi.org/10.3390/su9071176
Chicago/Turabian StyleTan, Lan, and Abdul Rahman. 2017. "From Technical Efficiency to Economic Efficiency: Development of Aza-Friedel–Crafts Reaction Using Phosphoric Acid Immobilized in Glycerol as a Sustainable Approach" Sustainability 9, no. 7: 1176. https://doi.org/10.3390/su9071176